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Facile single-step synthesis of pentaaryl-substituted pyrano[3,2-b]pyrrol-5(1H)-ones showing aggregation-induced emission
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-10-29 , DOI: 10.1039/d4qo01600a
Yongfeng Wang, Ruijun Chu, Yanxiao Wang, Mengyuan Zhou, Yuan Chen, Cheng Xu, Jingyu Sun, Guodong Yin

The continuing desire for multifunctional AIE materials has stimulated intensified research efforts to develop both innovative synthetic techniques and novel scaffolds. Herein, we report a new class of heterocyclic AIEgens, 1,2,3,6,7-pentaaryl substituted pyrano[3,2-b]pyrrol-5(1H)-ones, which contain an intriguing fused pyrrole/α-pyrone core. These structurally novel molecules were efficiently constructed via multicomponent reactions of easily accessible isatins, 2,3-diaryl cyclopropenones, and alkyl bromides in a single step under metal-free conditions. Subsequent late-stage modification of the resulting products was performed via the Suzuki–Miyaura coupling and reduction reactions. Furthermore, the HOMO/LUMO gaps were calculated and the single crystal structural analyses were conducted in order to gain deeper insights into the photophysical properties of these propeller-like AIEgens.

中文翻译:


五芳基取代的吡喃[3,2-b]吡咯-5(1H)-酮的简便单步合成显示聚集诱导的发射



对多功能 AIE 材料的持续需求激发了加大研究力度,以开发创新的合成技术和新型支架。在此,我们报道了一类新的杂环 AIEgens,1,2,3,6,7-戊酰取代的吡喃[3,2-b]吡咯-5(1H)-酮,它包含一个有趣的熔融吡咯/α-吡喃酮核心。在无金属条件下,通过易接近的蚂蚁素、2,3-二芳基环丙烯酮和烷基溴的多组分反应,一步有效地构建了这些结构新颖的分子。随后通过 Suzuki-Miyaura 偶联和还原反应对所得产物进行后期修饰。此外,计算了 HOMO/LUMO 间隙并进行了单晶结构分析,以便更深入地了解这些类似螺旋桨的 AIEgens 的光物理特性。
更新日期:2024-10-29
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